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As I’ve said since the moment his name first popped up this offseason, Ryan Dempster never seemed like a good fit for the Cubs. Yes, they need starters, and yes they could probably use a veteran leader or two. But the Cubs just sent Dempster away mid-season, he’ll be 36 next year, and he’s looking to cash in on what might be his last big contract. It was very hard to see the fit.

And it sounds like there won’t be a fit, as Ken Rosenthal reports that Dempster and the Boston Red Sox are close to a deal. There were previous reports that Dempster had turned down a two-year, $25 million from the Red Sox, so it’ll be interesting to see if he decided he couldn’t do better, or if they decided to up the offer.

The Red Sox had been connected to a number of starters in the mid-tier pitching market, so, if Dempster ends up going there, and if the Cubs weren’t ever really seriously in on Dempster, him signing there would have a slight positive impact on the Cubs’ chances with other starters in that range.

UPDATE: Rosenthal reports that it’s going to be two years and $26.5 million for Dempster, who obviously decided he’d settle for Boston if they could just bump their offer slightly. Best of luck to Dempster with the Red Sox.

1) Demp was effective last year.
2) Demp could *help* cure some of the club house issues they have had in recent years.

Cedlandrum

He didn’t help cure the clubhouse issues the Cubs had in the past.

ETS

Not the milton bradley year, but I think overall dempster is a net positive on the clubhouse.

Cedlandrum

I think you are right overall, but I doubt he can cure what ails them. Winning is the only thing that will cure the sawx.

ETS

agreed.

Jim L.

I think you are overestimating the impact of his impersonation of Will Ferrell impersonating Harry Caray – that act gets old fast.

ETS

My favorite dempster quotes

when asked how does one treat a strained lat?
“I take the Josh Beckett approach and try to get in as many rounds of golf as possible.”

When asked about a trade rumor on the internet.
“Well, if it’s on the internet then it must be true.”

JulioZuleta

He’s makng it so easy for me to root against him.

Diamondrock

Ugh. I live in Cambridge, MA these days, so I expect I’ll have to deal with some annoying crap if this goes through.

bloctoad

I thought he wanted to play for a *winning* team?

Chad

I think Demp would have been a great fit for the cubs on a 2 year- $20 mil deal possibly with option. And no- no trade clause. I think that was probably the biggest thing that would have kept the cubs and Dempster apart. Prior to the big Atl debacle I was certain the cubs would resign demp at the end of the year, but I think the whole shinanigins soured it for both sides. I think Demp would only be a fit for the cubs if they were allowed to flip him at the trade deadline for a guy like Delgado. Oh how I wish Delgado was a cub right now.

Curt

a fitting place for the douschenozzle to end up he’ll fit right in.

HateDemp

So happy he is (or near) gone. Hope he gets pounded next year.

HateDempMore

Wasn’t he gone at the trade deadline?

Timmy

If the Cubs had resigned him or traded for the homophobe I would not have watched games next season.

JR

If Bourne only gets a one year deal does the team taking him still have to give up a compensation pick?

cubfanincardinalland

Here is my Ryan Dempster story from a few years back. Was playing in a low limit $6-12 hold em poker game at the old President Casino on the St. Louis riverfront. Dempster came in after a ball game and started playing with a friend. We were chatting, and we asked him, don’t you make a lot of money, and we’re playing for like $100 pots in the game.
He laughed, and said, “I just want to take your money dudes.” He won the next hand, and proceeded to buy beers and shots for the whole table. He’s all right in my book.

Assman22

Marmol for Salty rumor floatng around this morning, unsure of how serious the two are about the deal, however the Cubs have been checking in on Salty all offseason…

TWC

… making the early offseason signing of Dioner Navarro all the more odd.

King Jeff

Eh, if they get Salty, then Castillo can go and catch every day in Iowa and improve his game calling and receiving skills.

How can he still be one of your favorites? Was it his high-jacking the Cubs organization in July last year? Did you enjoy his behavior? How does he have a reputation as a classy guy? Because he does some charity, factor everything in, the guy is a tool. He handled that situation so poorly last year, he screwed the Cubs. I hate that guy, he is going to get lit up there and he deserves it

MichiganGoat

If he struggles with the Red Sux the Boston media will blame Theo. I’m sure Nicky C is already meeting with Larry Lou on how blame Theo for any problems they have next year.

cRAaZYHORSE

No, Blame the Theo crap should have ended when the Redsox was able to unload 230 million dollars worth of contracts to the Dodgers.

Kevin B

I think Demp would have looked great in Milwaukee. He has a home in Chicago (had two) and could have come back to not only the National League but the same division he was comfortable and doing well in. Not sure I like it for him (but its his call of course) in Boston, tough division to pitch in and not a winning team, of course maybe he likes the tradition, Cubs, Red Sox, Fenway, Wrigley.

I do not buy this crap that he screwed the Cubs. He did no such thing. Plus the Cubs got Soriano, a better prospect then Delgado and better long term asset, for Maholm. Then they got Villanauva (spelling) a nice 3b prospect from the Rangers for Demp plus another decent pitching prospect. Great moves, it will turn out better for the Cubs.

I see his is critized for not being classy? Huh? Someone said “because he does charity work?” – Well YES that is part of it, he cared about the Cubs and the Community, was a leader in the Clubhouse and on the field. Went to the pen and kicked ass when he did not want to but the team needed him and came back a a starter and kicked ass when needed.
Class act all around. I wish him well.

Oh and for getting him back for 20 milion and 2 years like a commenter stated, that would have been terrific but he got a much better deal for 2 years and 26.5 and since he is coming to the twilight of his career he needs to do what he needs to do.

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